Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-butyl 4-(1-cyano-2-(4'-(isopropylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

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Reaction Steps

The mixture of (S)-tert-butyl 4-(1-amino-3-(4′-fluorobiphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate and (S)-tert-butyl 4-(1-amino-3-(4′-(isopropylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 4, step (i), 620 mg) in dichloromethane (15 mL) was treated with Burgess' reagent (462 mg) and the mixture was stirred at room temperature for 2 days. The reaction was absorbed onto silica and was purified by chromatography on silica eluting with 25% ethyl acetate in isohexane and then 50% ethyl acetate in isohexane to afford after evaporation of the relevant fractions (S)-tert-butyl 4-(1-cyano-2-(4′-fluorobiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (218 mg) and (S)-tert-butyl 4-(1-cyano-2-(4′-(isopropylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (300 mg).

Provenance & Evidence